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$2,500,000
993359 MLS
Set amid the bucolic farmland of Cutchogue, this rare 37+ acre Agricultural Conservation property offers exceptional scale, mature vines, and agricultural versatility. Approximately 20 acres are planted with established vineyard varietals, with the balance open for additional plantings or other permitted agricultural uses, including equestrian or cattle. A compelling opportunity for a vineyard enthusiast, farmer, hobbyist, or those seeking a substantial piece of North Fork farmland to steward and shape over time. The property includes a 2,700-square-foot cedar agricultural barn and three operational wells, with an agricultural license in place. Highly visible from Main Road and conveniently located near Cutchogue's farms, vineyards, beaches, restaurants, and village amenities.

37025 Main Road, Cutchogue
$949,000
3 Beds ⋅ 2 Baths ⋅ 987905 MLS
Welcome to your quintessential North Fork coastal retreat! Tucked away on a quiet, tree-lined street with peek-a-boo water views, just moments from pristine beaches and world-class vineyards, this 3-bedroom, 2-bath beach house blends relaxed vacation vibes with everyday comfort. The property has a new roof, new gas water heater and a bright, open-concept main floor featuring a cozy fireplace for breezy evenings, and a seamless flow for entertaining. Your updated chef's kitchen comes fully equipped with brand new Stainless Steel appliances, new refrigerator, dishwasher, range/oven and microwave. The serene primary suite boasts a private marble en-suite bath, while two additional bedrooms offer plenty of room for family, friends, or a remote workspace. The spacious basement has bonus areas for recreation, movies, games, and storage. This lovely retreat also offers plenty of room for your vehicles and toys as it has a heated-attached large spacious 2 car garage, and a separate single car garage. Step outside into your own private oasis with mature landscaping, a spacious patio, and plenty of room to add a custom swimming pool. You also have exclusive access to a resident-only private beach on the Mattituck Inlet, perfect for enjoying peaceful water views, kayaking, water sports, and sunset picnics. This charming home is a short walk to the marina, restaurant, bar, and live entertainment. Moreover, Mattituck’s own “Love Lane” is only a short walk or bike ride to enjoy some of the best the East End has to offer. Surrounded by the best local farm stands, shops, wineries and 5 minutes away from multiple marinas and beaches, this property is the ultimate North Fork escape—whether you are seeking a seasonal vacation getaway, an investment opportunity, or your forever home.

680 Westview Drive, Mattituck
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 986519 MLS
Masterfully built, blending timeless design with modern comforts and expert craftsmanship, creating an undeniable sense of harmony and place, on a lovely 1/2-acre level lot, just moments from Love Lane, Strong's Marina and Bailey Beach 3000 Grand Ave. is the perfect North Fork country house. Clad in classic cedar shingles and anchored by a welcoming front porch, this home immediately feels like the perfect North Fork retreat. Inside, uplifting natural light pours through expansive windows, illuminating an elegant foyer and dining room. The kitchen supports both everyday living and effortless entertaining, featuring Quartz countertops, stainless steel appliances, drawer microwave and a generous island. The first floor also includes a lovely private ensuite bedroom. On the second floor we find the primary suite, a serene sanctuary, featuring a spa inspired bath. Two additional guest bedrooms share this level. The exterior is designed for outdoor enjoyment featuring a heated saltwater pool with expansive paver patio. New construction with completion in Fall 2026

3000 Grand Avenue, Mattituck
$2,995,000
4 Beds ⋅ 5 Baths ⋅ 984475 MLS
CHIC, SLEEK, AND COMPLETELY UNIQUE - This industrial chic modern hits every box. Open concept living, radiant heated concrete floors throughout. A floating fireplace and walls of glass bringing the outdoors straight into the everyday. The living space spills out to the private heated Gunite saltwater pool, expansive patio and outdoor shower - creating an indoor-outdoor flow that feels polished, relaxed, and spa-like. A covered patio provides space for al-fresco dining. With 4 bedrooms, 4.5 baths, a dedicated laundry room, and parking for 5 cars between the garage and carport, this property delivers an elevated design, completely unique to the North Fork on every level. Stroll to restaurants, farm stands, and into town. Easy in and out to NYC and surrounded by beaches and renowned vineyards!

2050 Depot Lane, Cutchogue
$5,925,000
4 Beds ⋅ 5 Baths ⋅ 972084 MLS
Cutchogue Showstopper. Perched atop a 55-foot bluff overlooking the Long Island Sound, this extraordinary Barnes Coy designed waterfront home offers rare architectural pedigree and an unrepeatable setting. Designed by Barnes Coy Architects, the award-winning firm known for some of the East End’s most distinctive modern residences, this 4,200 SF jewel box estate is set within a private neighborhood with its own park and private stairs to the beach. Filled with natural light and premium finishes, the home features polished limestone floors with radiant heat, two primary ensuite bedrooms with ample closet space, smart home technology controlling lights, blinds, temperature, and front gate; solar panels for energy efficiency, and a full-house generator. The lower level with full bath offers flexible space for a media room, gym, office, or guest overflow. An attached two-car garage is also included. Outside, a heated saltwater gunite pool, hot tub, 1000 sf rooftop deck, firepit, and back lawn create an exceptional waterfront setting for entertaining or quiet enjoyment. Enjoy breathtaking sunsets from the rooftop deck or pool, practice yoga with wide water views, or watch seals gather on the rocks below. An outdoor shower with interior and exterior access adds ease after the beach or pool, and there is room to create an outdoor dining and kitchen area. A truly architecturally significant North Fork offering with exceptional water views, spectacular sunsets, privacy, and a setting that simply cannot be recreated.

445 Glen Court, Cutchogue
$4,350,000
3 Beds ⋅ 2 Baths ⋅ 976938 MLS
MAGIC ON OREGON ROAD Romance, Elegance and Timeless beauty over 38 acres on bucolic Oregon Road, you couldn't ask for anything more! 36 acres of DRS land which includes 30 planted acres of grape vines, deer fencing and bird netting, irrigation in place for an additional 2-3 acres of planting and a potential wine tasting area. The updated vintage farmhouse rests on 2 acres of DRI land and features 3 bedrooms, 2 bathrooms, sun drenched open floor plan, eat-in-kitchen, dining area, sitting area with reading nook, living room with a fireplace. Step outside and enjoy lush landscape surrounding the pool, outdoor shower and vineyard views! Surrounded by award winning North Fork wineries, restaurants, farm stands, boating & great shopping.

2600 Oregon Road, Mattituck
$2,479,000
4 Beds ⋅ 5 Baths ⋅ 973930 MLS
Welcome to 675 Pine Tree Rd, a brand-new coastal retreat nestled on a half acre in Cutchogue. Enjoy the rare convenience of dropping your paddle board in creek at the end of the street, strolling around the corner to Broad Cove Marina or heading down the road to Causeway beach just .8 miles away. This beautifully crafted 4-bedroom 5-bathroom luxury residence offers 3,200 s.f. of thoughtfully designed living space flooded with light over size windows and high ceilings, elegant millwork and 3-1/2" white oak flooring throughout. The heart of the home is a stunning chef’s kitchen featuring quartz counter tops, custom cabinetry and Thermador appliances opening to the main living area, perfect for entertaining and enjoying the North Fork lifestyle. The home offers two primary suites, providing exceptional flexibility for owners and guests. A spacious first floor junior suite with cathedral ceiling offers comfort and privacy, while the second-floor primary suite features a tray ceiling, large walk-in shower, soaking tub and his/hers walk in closets. The second floor has a sitting area and two additional en-suite bedrooms with vaulted ceilings and walk in closets. Outdoors, beautiful lush landscaped grounds surround a saltwater heated pool and stone patio, ideal for summer gatherings and entertaining. A rare opportunity to own a brand new home in a premier location with completion expected in July 2026.

675 Pine Tree Road, Cutchogue
$879,000
3 Beds ⋅ 2 Baths ⋅ 972288 MLS
Set against a backdrop of preserved farmland, this exquisite move in ready 3-bedroom, 2-bath Mattituck retreat captures the essence of North Fork living with waterviews, farm views and unforgettable, color-drenched sunsets. Designed with an open floor plan, the home is filled with natural light and offers effortless flow for everyday living and entertaining featuring a wood burning fireplace with wood burning cast-iron stove inside. A newly updated kitchen with stainless steel appliances, real wood cabinets and beautifully renovated bathrooms elevate the interior with modern comfort and style. Step outside to an expansive upper deck and lower patio—ideal vantage points to take in the peaceful agricultural landscape and evening skies. Perfectly positioned, enjoy easy access to Love Lane’s beloved boutiques, cafe's, and wineries, while Bailee's Beach is just moments away for sun-soaked days by the water. Located .6 miles from the LIRR and Hampton Jitney. Exceptional living at its finest, this home boasts wood floors and Anderson Windows throughout, brand new AC units, newer boiler, updated septic, new Anderson front door, public water, 2023 new chimney lining and chimney refaced, newer appliances 2019-2024, newer leaf guard gutters and propane for gas cooking. Whether you’re seeking a full-time residence or a weekend escape, this property delivers privacy, proximity, and picturesque beauty in one of the North Fork’s most sought-after locations. This listing may include images that have been digitally altered or virtually staged.

540 Conklin Road, Mattituck
$875,000
970333 MLS
Beautiful 5.84 acre parcel located on the heart of the North Fork. Zoned residential (AC), this property offers endless potential for a private home or vacation retreat. The expansive lot features serene natural surroundings, ample space for development and is ideal for creating your dream property. Whether you're looking for a peaceful lifestyle or an investment opportunity, this property combines North Fork charm with versatile residential zoning.

15690 County Road 48, Cutchogue
$2,100,000
5 Beds ⋅ 5 Baths ⋅ 952621 MLS
Introducing a rare opportunity to build your custom dream home at 2200 Laurel Trail, ideally situated within the private Laurel Links community in the heart of Laurel’s sought after North Fork. This to be built residence offers buyers the ability to personalize finishes, layout details, and design elements while securing brand-new construction in an exceptional golf course setting. Occupying a prime .70 acre golf course lot, perfectly positioned backing directly to the fairway, the property offers sweeping views, exceptional privacy, and a serene backdrop of manicured greens. There is ample room for a pool and outdoor entertaining space, allowing you to create a true resort style backyard. Residents of Laurel Links enjoy exclusive access to community amenities including a clubhouse with recreation facilities, resort style pool, tennis courts, and a premier golf course all within a secure, beautifully maintained enclave. Located just moments from North Fork beaches, renowned vineyards, farm stands, and charming local shops, this offering combines lifestyle, luxury, and location. Enjoy the benefits of new construction and the rare opportunity to customize every detail. Now is the time to design and build a home that truly reflects your vision in one of Laurel’s most desirable communities.

2200 Laurel Trail, Laurel
$999,000
962608 MLS
Nestled along the picturesque shores of Long Island Sound, this exquisite property offers a rare opportunity to indulge in the epitome of waterfront living. Boasting panoramic views of the glistening waters and stunning sunsets, this parcel is raised and setback as to where you have the perfect sanctuary of tranquility and elegance. Beach access, world renowned vineyards, farmers markets, shops etc all a stones throw away. There are three cottages all require extensive renovation. Dock is also permitted and ready to go!! Set your appointment today as this will not last long!

1775 Naugles Drive, Mattituck
$399,000
957255 MLS
Tucked away on a serene cul-de-sac in the heart of Mattituck, this prime, shy wooded acre offers a rare blend of privacy, natural beauty, and opportunity. Gently rolling terrain creates the perfect canvas for your custom retreat, while expansive sunset views over neighboring wetlands provide a breathtaking daily backdrop. With the DEC permit and Southold Town Trustee approvals renewals in progress, and the Board of Health permit in place, the groundwork has already been laid for your vision to come to life. Imagine designing and building your ideal North Fork home in this peaceful, sought-after setting.

955 Blossom Bend, Mattituck
$660,000
3 Beds ⋅ 2 Baths ⋅ 954672 MLS
This colonial-style home features three bedrooms, two full baths, an eat-in kitchen, and driveway parking. The information provided is estimated to the best of our abilities at this time.

24635 Main Road, Cutchogue
$525,000
953624 MLS
Shy half acre lot located in the heart of the North Fork - close to beaches, wineries, restaurants, boating and more! Great spot to build a year round or vacation home.

725 Youngs Avenue, Mattituck
$2,299,000
3 Beds ⋅ 3 Baths ⋅ 943316 MLS
Set along one of Mattituck’s most sought-after waterfront enclaves, 2280 Deep Hole Drive offers a rare opportunity to own an exquisite waterfront residence newly built in 2022, encompassing 3,000 square feet of thoughtfully designed living space with exceptional deepwater dockage and direct access to Peconic Bay. Perfectly suited for the boating enthusiast, the property features approximately 130 feet of deepwater frontage on Deep Hole Creek and a substantial dock capable of accommodating two vessels up to 36 feet, complete with electric and water, providing protected, convenient access to the bay and beyond. The home features 9-foot ceilings on the main level, an open-concept layout filled with natural light, expansive water views, and refreshing bay breezes throughout. At the heart of the home is a custom chef’s kitchen appointed with premium, professional-grade appliances, high-end finishes, and a large center island ideal for entertaining and everyday living. The kitchen flows seamlessly into the dining and living areas, where a gas fireplace anchors the space with warmth and ambiance while framing serene water views. Sliding doors from the main living areas open to a waterside deck and balcony, creating an ideal setting for alfresco dining or relaxing in the spa-style hot tub overlooking the water. The first-floor primary suite offers a private retreat with an en-suite bath, and then there are 3+ additional spacious bedrooms, dedicated workstation areas, and 2.5 baths that provide flexibility and comfort. The full walk-out daylight basement provides expansive storage and the potential for a gym, workshop, or recreational space. Built with enhanced features for comfort and efficiency, the home includes a Navien tankless hot water system, 1,000-gallon propane tank, thermal windows, updated systems throughout, and a whole-house Generac generator for added peace of mind. Outdoors, there is room for a pool, and the waterfront setting creates an exceptional lifestyle opportunity for boating, fishing, paddleboarding, and entertaining by the water. Ideally located less than one mile from Love Lane and just minutes to local vineyards, farm stands, beaches, parks, and acclaimed North Fork dining, 2280 Deep Hole Drive is more than a home—it is a complete waterfront lifestyle defined by modern design, flexible living spaces, coveted dockage, and the unmistakable charm of Mattituck’s North Fork. Includes an option to purchase furnishings. Nearby Pool Club Membership available at Strong’s Water Club and Marina. This listing may include images that have been digitally altered or virtually staged.

2280 Deep Hole Drive, Mattituck
$1,495,000
3 Beds ⋅ 2 Baths ⋅ 932413 MLS
17525 County Rd. 48 (aka Middle Rd). Currently being used as a "tree farm", large farmhouse w/high ceilings, open living/dining area, craft room, den and office space. First floor full bath, full row of storage closets. Second floor offers large primary bedroom with high ceilings & 2 additional bedrooms, full bath. Inground pool, large patio area, huge accessory building with large overhead door, 2.06 acres (150 x 600) with partial irrigation zoned AC Agriculture Conservation (Residential). Endless possibilities with large outbuilding for the hobby enthusiast, country farmer or one looking for a serene lifestyle amongst the beautiful North Fork surroundings.

17525 County Road 48, Cutchogue
$3,500,000
929435 MLS
Waterfront Opportunity on the Long Island Sound! Discover the rare chance to own prime waterfront land on esteemed Oregon Road in Cutchogue, AKA the Sunniest spot in New York. Headlining 2.72 acres and over 183 feet of direct water frontage on the Long Island Sound. This exceptional property offers sweeping, unobstructed water views and the serenity of coastal living. Whether you envision a private estate, vacation retreat, or future development, this parcel provides endless potential. Enjoy breathtaking sunsets, gentle sea breezes, and a front-row seat to one of the most coveted shorelines in the region. A truly remarkable opportunity to build your dream home on the North Fork. Price is for land only.

6121 Oregon Road, Cutchogue
$4,995,000
6 Beds ⋅ 7 Baths ⋅ 894818 MLS
Brand new exquisite waterfront 6 bedroom, 7 bathroom home set on 1.33 acres along coveted Mattituck Inlet in the heart of the North Fork, this exceptional waterfront retreat spans approximately 5,920 square feet of refined living space, blending classic Hamptons-style cedar-shingle architecture with a sophisticated, contemporary interior. Designed for both elegance and everyday comfort, the home features an airy open-concept layout anchored by a dramatic great room with soaring ceilings, expansive Andersen 400 Series double-hung windows, and walls of glass framing panoramic water views. A Heat & Glo 36” propane fireplace with tranquil surround, LED lighting, fan blower, and multi-function remote adds warmth and ambiance. The chef’s kitchen is a true showpiece, appointed with full overlay cabinetry with glass-top cabinets extending to the ceiling, quartz countertops, and a premium appliance suite including a 48” Sub-Zero refrigerator, 48” Wolf gas range, 30” Wolf double wall oven, 24” Wolf microwave, and 24” Miele dishwasher—all stainless steel. The kitchen flows seamlessly into the dining area and outdoor entertaining spaces. The primary suite offers a spa-inspired retreat with radiant electric floor heating in the primary and junior primary baths, private terrace access, and serene water views. Wide-plank 7” plain-sawn white oak flooring runs throughout, enhancing the home’s warm yet modern aesthetic. Additional bedrooms are generously sized and thoughtfully designed for privacy and comfort. Outdoor living is exceptional, featuring a heated 20’ x 40’ gunite saltwater pool with jacuzzi, surrounded by imported Marmiro Stone (Afyon Cloud) patios, a mahogany primary deck, covered porch, and landscaped grounds serviced by a 10-zone Hunter irrigation system. The property includes metal and cedar fencing, a private dock, and direct waterfront access—ideal for boating and waterside living. Additional highlights include state-of-the-art, energy efficient, multi zone HVAC (every bedroom and common area has its own thermostat - the system has multiple fans for dedicated zones), central air, public water, septic system, a two-car garage, cedar shingle roof and siding with white double-dipped finish. Surrounded by vineyards, farm stands, and pristine North Fork beaches, this extraordinary waterfront estate delivers modern luxury, timeless craftsmanship, and the relaxed elegance of Long Island’s wine country—an unparalleled opportunity for refined coastal living. This listing may include images that have been digitally altered or virtually staged.

2590 Cox Neck Road, Mattituck
$2,549,000
4 Beds ⋅ 3 Baths ⋅ 908511 MLS
Experience the ultimate in North Fork waterfront living at this captivating 4-bedroom, 3-bathroom retreat on the Peconic Bay. Featured in The New York Times and Rue Magazine, this home was designed by the renowned firm Hyphen & Co. with the vision of making every day feel like a vacation. Set on prime private bay frontage, the residence was thoughtfully crafted to maximize water views from nearly every room. The open-concept main level is the heart of the home, with a modern chef’s kitchen featuring stainless steel appliances, sleek white cabinetry, light countertops, and a spacious island that doubles as a breakfast bar. The adjoining dining area and sun-filled living room create an effortless flow, with large windows and sliders that frame sweeping vistas across the bay to Robins Island and Southampton. The primary suite is a true sanctuary with its own balcony overlooking the water—perfect for sunrise coffee or sunset cocktails. Three additional bedrooms and two well-appointed baths provide plenty of space for family and guests. Each detail, from the wood-finished floors to the custom fixtures, reflects a balance of elegance and comfort. Step outside to an expansive waterside deck designed for unforgettable entertaining, from al fresco dining to nights by the fire pit. With direct access to the bay, enjoy swimming, kayaking, paddleboarding, boating, and fishing just steps from your door. Located minutes from Love Lane, vineyards, farm stands, and fine dining, this property offers the best of North Fork lifestyle—charm, convenience, and unmatched natural beauty. Furnishings included in the sale. Recent premium updates include New roof(full), New upper and lower decks, New siding and upgraded window surrounds, New driveway, New bulkhead cap, New rugs in primary and guest bedrooms, New electric shades, New outdoor composite lighting. Private beach, full service marina and pool membership club just around the corner and the ability to moor your boat right out front.

4415 Camp Mineola Road, Mattituck
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 907439 MLS
Welcome to Lion’s Gate on the Sound, a premier waterfront estate set on over 3 private, gated acres along the Long Island Sound in Mattituck. This move-in-ready sanctuary blends timeless architecture with modern luxury, offering unmatched privacy and sweeping coastal views. A newly resurfaced driveway leads through electronic gates to beautifully lit grounds featuring a restored gazebo, lush lawns, and thoughtful landscaping. Inside, the home shines with freshly refinished hardwood floors, custom details, and a reimagined primary suite with spa-like finishes. Smart-home automation, new TVs, and elegant upgrades enhance everyday living. The finished lower level offers a professional gym, billiard room, and custom bar, while the upgraded garage with epoxy floors and smart tech is ideal for car enthusiasts. Outdoors, enjoy a new dining pavilion, full irrigation, and multiple vantage points for stunning sunsets over the Sound. Perfectly located near vineyards, farm stands, and charming village life, Lion’s Gate on the Sound is more than a home, it’s a legacy estate of luxury, seclusion, and natural beauty. Seller working to obtain pool permit.

3875 Hallock Lane, Mattituck
$705,000
3 Beds ⋅ 2 Baths ⋅ 906405 MLS
Step into this cute and cozy country colonial updated and renovated inside and outside in 2023. Anderson windows on the outside for keeping the house toasty and warm. SS appliances in the country kitchen with hardwood floors on the main floor. Three bedrooms upstairs including a full hall bathroom. There is also a wood burning fireplace in the living room to add to the country flavor. Full unfinished basement with an outside entrance to add to your living space. And the location is close to all including shops with the flavor of a truly historic area.! Country living at its best! .

30170 Main Road, Cutchogue
$2,075,000
L3530560 MLS
Prime Development Parcel In Center of Mattituck's Burgeoning Business District! Multiple Business, Residential & Mixed Use Possibilities. 5 Buildings Possible As of Right. Commercial Listing MLS# 3530701, Additional information: Minimum Plot Size:10000

385 New Suffolk Avenue, Mattituck
$1,999,000
L3562073 MLS
Cutchogue, North Fork - expired Trustee's permit to construct a single-family waterfront residence on superb soundfront lot with incredible Waterview and convenient location with access to all of the best of the North Fork.... Located north of Oregon Road, among the broad fields and vineyards is the site for the development of your North Fork dream home, with 100 feet on the sound and your own beach. Paved road, association beach access (private stairs permitted), water/electric at street. Sit down with your designer/architect and plan your future now - or acquire as an investment. Ass'n stairs to beach below a few doors away.

895 Glen Court, Cutchogue

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.